look up any word, like boo:
 
1.
1. To be without a roof

2. Fierce!
"You be roofless... You may have a house but you have no roof, so bitch when it rain, you gon get wet. Therefore you be roofless."

"Damn girl! Your Roofless"
by thanalicious27 October 18, 2011
 
2.
The slang pronunciation of "Ruthless".

The term "Roofless" is used to define two (2) types of people:

1. Acknowledge someone who has the ability to make very harsh & demeaning personal insults against another person and not have any remorse, instead basking in the glory. (see example 1)

2. Praise a person before or after a dare, to whom the person is willing to take a huge risk that is highly embarrasing to themselves or another person. (see example 2)

When applied in a real-life situation, it is spoken or shouted AFTER the person has made the comment or accepted/completed the demoralising challenge (as given in the example).
Pronounced "roof" ~ "less"

Example 1:
Jack: Hey have you guys seen the new Terminator movie?

Daniel: No, but have you seen the one starring you in it?

Jack: What?

Daniel: ITS CALLED THE VIRGINATOR!!

Everyone Else (to Daniel): ROOOFLESSSSSSS!!!!!

Example 2:
Everyone: Oy go steal that bottle of water and take a picture of yourself with it.

Jackson: I'm not going to do that...

Everyone: PUSSY!

Jackson: Everyone would know what that is... except Jack...

Everyone (except Jack): ROOFLESSSSSS!!!

Jackson: YOU KNOW WHAT, FINE! I'll steal it.

Everyone: ROOFLESSSSSSSSSS!!!!
by crew2010 March 22, 2011